d-1,2,3,4-tetrahydro-2-naphthoic acid methyl ester | 53319-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: d-1,2,3,4-tetrahydro-2-naphthoic acid methyl ester
• 英文别名: methyl (2R)-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 53319-10-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: IAJCTSSNCSYJPW-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  d-1,2,3,4-tetrahydro-2-naphthoic acid methyl ester 在 正丁基锂 、 zinc borohydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， 反应 4.75h， 生成
  参考文献：
  名称：

  Structure-activity studies of configurationally rigid arylprostaglandins

  摘要：

  Potent, albeit nonselective, smooth-muscle stimulant activity has been previously reported for 16-phenoxy- and 17-phenylprostaglandins, a finding that led to the design and development of the tissue-selective uterine stimulant sulprostone. As an extension of this work, analogues incorporating the 16-phenoxy and 17-phenyl substituents into the rigid indanyl, tetrahydronaphthyl, dihydrobenzofuryl, and dihydrobenzopyranyl ring systems were prepared and evaluated for uterine stimulant activity in vitro and diarrheal effects in vivo. Since these cyclic groups, with the exception of the indanyl, contain a chiral center, both optical antipodes were prepared. These studies demonstrate that ring size, heteroatom, and absolute configuration at C-16 are important determinants for potency and selectivity.

  DOI：

  10.1021/jm00357a004
• 作为产物：
  描述：

  1,2,3,4-四氢-2-萘甲酸 在 硫酸 作用下， 生成 d-1,2,3,4-tetrahydro-2-naphthoic acid methyl ester
  参考文献：
  名称：

  Structure-activity studies of configurationally rigid arylprostaglandins

  摘要：

  Potent, albeit nonselective, smooth-muscle stimulant activity has been previously reported for 16-phenoxy- and 17-phenylprostaglandins, a finding that led to the design and development of the tissue-selective uterine stimulant sulprostone. As an extension of this work, analogues incorporating the 16-phenoxy and 17-phenyl substituents into the rigid indanyl, tetrahydronaphthyl, dihydrobenzofuryl, and dihydrobenzopyranyl ring systems were prepared and evaluated for uterine stimulant activity in vitro and diarrheal effects in vivo. Since these cyclic groups, with the exception of the indanyl, contain a chiral center, both optical antipodes were prepared. These studies demonstrate that ring size, heteroatom, and absolute configuration at C-16 are important determinants for potency and selectivity.

  DOI：

  10.1021/jm00357a004

文献信息

• Structure-activity studies of configurationally rigid arylprostaglandins
  作者：Thomas K. Schaaf、M. Ross Johnson、Jay W. Constantine、Jasjit S. Bindra、Hans Juergen Hess、Walter Elger

  DOI：10.1021/jm00357a004

  日期：1983.3

  Potent, albeit nonselective, smooth-muscle stimulant activity has been previously reported for 16-phenoxy- and 17-phenylprostaglandins, a finding that led to the design and development of the tissue-selective uterine stimulant sulprostone. As an extension of this work, analogues incorporating the 16-phenoxy and 17-phenyl substituents into the rigid indanyl, tetrahydronaphthyl, dihydrobenzofuryl, and dihydrobenzopyranyl ring systems were prepared and evaluated for uterine stimulant activity in vitro and diarrheal effects in vivo. Since these cyclic groups, with the exception of the indanyl, contain a chiral center, both optical antipodes were prepared. These studies demonstrate that ring size, heteroatom, and absolute configuration at C-16 are important determinants for potency and selectivity.